Coastal cruisers and racers experience a range of temperatures and weather, so crossover garments that can be layered—or not—and can be worn racing or cruising will top the list. Look for lightweight outer layers and cozy, warm base- and mid-layers that won’t trap air and moisture. The same three-layer materials used in bluewater gear are now beginning to make inroads in coastal gear as well. But a set of foulies made with a quality two-layer fabric will still keep you plenty comfortable without breaking the bank.

It all started when I entered SAIL’s Crew for a Day contest on Facebook. As per the rules, I wrote a 50 word essay about one of my favorite moments while sailing. A cocky man would follow this statement with “… and I won.” I prefer to look at it as the payoff for some unremembered bet I made with Karma - while doubling down. Photos by Rob Rich